CN115028647A - Fused ring triazole bislactam-based non-fullerene acceptor material and preparation method and application thereof - Google Patents
Fused ring triazole bislactam-based non-fullerene acceptor material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a condensed ring triazole dilactam non-fullerene acceptor material and a preparation method and application thereof. The condensed ring triazole dilactam non-fullerene acceptor material comprises a condensed ring triazole dilactam central core and electron-deficient end groups, wherein the condensed ring triazole dilactam central core is of a nitrogen bridge trapezoidal condensed ring structure, and the electron-withdrawing end groups are connected to two ends of the central core. The receptor material has good solubility and is easy to process into a film. The organic/polymer solar cell and the organic photodetector prepared by taking the condensed ring triazole bislactam group non-fullerene acceptor material as the active layer both have excellent performance, the energy conversion efficiency of the organic photovoltaic cell is more than 11 percent, and the dark current density of the organic photodetector is lower than 10 ‑8 mA/cm 2 To fully showThe non-fullerene acceptor material has wide market prospect in the fields of organic photovoltaics, logic complementary circuits, organic photodetectors and the like.
Description
Technical Field
The invention belongs to the technical field of organic semiconductor materials, and particularly relates to a condensed ring triazole bislactam-based non-fullerene acceptor material and a preparation method and application thereof.
Background
In recent years, non-fullerene acceptor materials have been developed, the efficiency of organic/polymer solar cells with efficient single-layer heterojunction reaches more than 16% (Sci China Chem,2019,62: 746-. However, the acceptor materials have the problems of poor stability, shallow Highest Occupied Molecular Orbital (HOMO) energy level, low open-circuit voltage, few matching types with donor materials and the like. Therefore, the search for new design strategies, and the search for new receptor building blocks, remains one of the effective approaches to solve these problems.
The bislactam derivative is an electron acceptor unit which is rich in heteroatoms, strong in electron affinity and good in coplanarity, and is widely used for developing n-type transmission materials (org. Lett.2017,19, 3275-3278.). However, introduction of fused ring triazole bislactam units into non-fullerene acceptor materials is rarely reported.
Disclosure of Invention
Aiming at the problems of poor stability, shallow HOMO energy level, low open-circuit voltage, few matching types with donor materials and the like of organic acceptor materials in the existing organic/polymer solar cell, the invention aims to provide a condensed ring triazole bislactam group non-fullerene acceptor material and a preparation method and application thereof.
The invention aims to provide a novel fused ring triazole bislactam-based non-fullerene acceptor material which is good in stability, higher in open-circuit voltage, higher in photoelectric conversion efficiency and lower in dark current.
The invention also aims to provide a preparation method of the fused ring triazole bislactam group non-fullerene acceptor material.
The invention further aims to provide application of the fused ring triazole bislactam group non-fullerene acceptor material in organic/polymer solar cells and organic photodetectors.
The invention relates to an organic/polymer solar cell and organic photodetector receptor material, in particular to a fused ring triazole bislactam-based non-fullerene receptor material, a preparation method thereof and application thereof in an organic/polymer solar cell and an organic photodetector.
The purpose of the invention is realized by at least one of the following technical solutions.
The invention provides a fused ring triazole bislactam non-fullerene acceptor material, which has a structural formula shown as the following (formula (I)):
wherein R is 1 Is C 1 -C 20 Alkyl groups of (a);
ar is a thiophene group, a bithiophene group or a bithiophene derivative group;
EG is any one of the following groups:
wherein R is 2 Is a hydrogen atom, a halogen substituent, C 1 -C 20 Alkyl of (C) 1 -C 20 Alkoxy or cyano of (a).
Further, Ar is the following group:
the dotted line is the connection position;
the invention also provides a preparation method of the fused ring triazole dilactam non-fullerene acceptor material, which comprises the following steps:
(1) under the protection of nitrogen, reacting a condensed ring triazole compound A with N-chlorosuccinimide (NCS) to obtain a compound B; the structural formulas of the condensed ring triazole compound A and the compound B are respectively as follows:
wherein R is 1 The definition of (a) is the same as the above definition;
(2) under the protection of nitrogen, reacting compound B with propyl chloroformate to obtain compound C, wherein the structural formula of the compound C is as follows:
wherein R is 1 Is as defined above;
(3) reacting the compound C with ammonium formate under the action of a palladium-carbon catalyst to obtain a compound D, wherein the structural formula of the compound D is as follows:
wherein R is 1 The definition of (a) is the same as the above definition;
(4) under the protection of inert gas, reacting the compound D with liquid bromine to obtain a compound E, wherein the structural formula of the compound E is as follows:
wherein R is 1 The definition of (a) is the same as the above definition;
(5) and (2) carrying out hydrolysis reaction on the compound E and sodium hydroxide to obtain a compound F, wherein the structural formula of the compound F is as follows:
wherein R is 1 The definition of (a) is the same as the above definition;
(6) reacting the compound F with oxalyl chloride and N-alkyl thiophene derivative-3-amine to obtain a compound G, wherein the structural formula of the compound G is as follows:
wherein R is 1 And Ar is as defined above;
(7) compound G with Tricyclohexylphosphine fluoroborate (PCy) 3 ·HBF 4 ) And palladium acetate and cesium carbonate to obtain a compound H, wherein the structural formula of the compound H is as follows:
wherein R is 1 And Ar is as defined above;
(9) carrying out Vilsmeier-Haack reaction on the compound H to obtain a compound I, wherein the structural formula of the compound I is as follows:
wherein R is 1 And Ar is as defined above;
(10) reacting the compound I with EG ketone through Knoevenagel to obtain a target fused ring triazole bislactam group non-fullerene receptor material;
the EG ketone is any one of the following structures:
wherein R is 2 Is a hydrogen atom, a halogen substituent, C 1 -C 20 Alkyl of (C) 1 -C 20 Alkoxy or cyano of (a).
The invention provides a preparation method of a fused ring triazole bislactam group non-fullerene acceptor material, which specifically comprises the following steps:
(1) uniformly mixing a fused ring triazolyl compound A, N-chlorosuccinimide (NCS) and a chloroform solvent, stirring at room temperature for reacting for 1-24 hours, and purifying reaction liquid to obtain a compound B;
(2) uniformly mixing a compound B, a 2,2,6, 6-tetramethyl piperidyl lithium chloride magnesium chloride compound and a tetrahydrofuran solvent, dissolving propyl chloroformate in a dried tetrahydrofuran solution after the reaction is finished, adding the propyl chloroformate into the reaction in batches, and purifying the reaction solution obtained after the reaction is finished to obtain a compound C;
(3) uniformly mixing the compound C, ammonium formate, a palladium-carbon catalyst and an ethanol solvent, refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, and purifying reaction liquid to obtain a compound D;
(4) uniformly mixing the compound D, liquid bromine and a trichloromethane solvent, refluxing, stirring, reacting for 1-24 hours, cooling to room temperature, and purifying reaction liquid to obtain a compound E;
(5) uniformly mixing the compound E, sodium hydroxide, ethanol, tetrahydrofuran and water, then refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, adding hydrochloric acid into reaction liquid for acidification, and purifying to obtain a compound F;
(6) uniformly mixing a compound F, oxalyl chloride, dichloromethane and a small amount of N, N' -dimethylformamide solvent, stirring at room temperature for reaction for 1-24 hours, removing the solvent, adding N-alkylthiophene derivative-3-amine, triethylamine and dichloromethane solvent, uniformly mixing, stirring at room temperature for reaction for 1-24 hours, and purifying to obtain a compound G;
(7) compound G, tricyclohexylphosphine borofluoride (PCy) 3 ·HBF 4 ) Uniformly mixing palladium acetate, cesium carbonate and an N, N' -dimethylformamide solvent, refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, and purifying a reaction solution to obtain a compound H;
(8) uniformly mixing a compound H, phosphorus oxychloride and an N, N' -dimethylformamide solvent, refluxing, stirring, reacting for 1-24 hours, cooling to room temperature, and purifying reaction liquid to obtain a compound I;
(9) uniformly mixing the compound I, EG ketone, pyridine and a chloroform solvent, refluxing, stirring, reacting for 1-24 hours, cooling to room temperature, and purifying reaction liquid to obtain the target fused ring triazole bislactam non-fullerene acceptor material.
Further, the molar ratio of the condensed ring triazole-based compound A to N-chlorosuccinimide (NCS) in the step (1) is 1: 1-100;
further, the molar volume ratio of the condensed ring triazole-based compound A in the step (1) to the chloroform solvent is 1mol: 0.01-1L;
further, the molar ratio of the compound B in the step (2) to the 2,2,6, 6-tetramethyl piperidyl magnesium chloride lithium chloride complex is 1:2-100,
further, the molar ratio of the compound B to the propyl chloroformate in the step (2) is 1: 2-100;
further, the molar volume ratio of the compound B in the step (2) to the tetrahydrofuran solvent is 1mol: 0.01-1L;
further, the temperature of the first reaction in the step (2) is-20 to-30 ℃, the reaction time is 1 to 24 hours, the temperature of the second reaction is normal temperature, and the reaction temperature is 1 to 24 hours.
Further, step (3) said compound C: ammonium formate: the mole ratio of the palladium carbon catalyst is 1: 2-100: 0.01-0.1;
further, the molar volume ratio of the compound C in the step (3) to the ethanol solvent is 1mol: 0.01-1L;
further, the molar ratio of the compound D to the liquid bromine in the step (4) is 1: 2-100;
further, the molar ratio of the compound D to the liquid bromine in the step (4) is 1: 2-100;
further, the molar volume ratio of the compound D in the step (4) to the chloroform solvent is 1mol: 0.01-1L;
further, the molar ratio of the compound E to the sodium hydroxide in the step (5) is 1: 2-100;
further, step (5) said compound E: ethanol: tetrahydrofuran: the molar volume ratio of the water solvent is 1mol:0.01-1L:0.01-1L: 0.01-1L;
further, step (6) said compound F: the mole ratio of oxalyl chloride is 1: 2-100;
further, the compound F of step (6): the mol ratio of the N-alkyl thiophene derivative group-3-amine is 1: 2-100;
further, the molar volume ratio of the compound F in the step (6) to the dichloromethane solvent is 1mol: 0.01-1L;
further, the molar volume ratio of the compound F in the step (6) to the triethylamine solvent is 1mol: 0.01-1L;
further, step (7) said compound G: tricyclohexylphosphine fluoroborate (PCy) 3 ·HBF 4 ): palladium acetate: the mol ratio of the cesium carbonate is 1: 2-100: 2-100: 2-100: 2-100;
further, the molar volume ratio of the compound F in the step (7) to the N, N' -dimethylformamide solvent is 1mol: 0.01-1L;
further, the molar ratio of the compound H to the phosphorus oxychloride in the step (8) is 1: 1-100;
further, the molar volume ratio of the compound H in the step (8) to the N, N' -dimethylformamide solvent is 1mol: 0.01-1L;
further, the molar ratio of the compound I to EG ketone in the step (9) is 1: 3-100;
further, the molar ratio of the compound I to the pyridine in the step (9) is 1: 1-100;
further, the molar volume ratio of the compound H in the step (9) to the chloroform solvent is 1mol: 0.01-1L;
further, in the steps (3) to (5) and (7) to (9), the reaction temperature was 60 to 200 ℃ with stirring under reflux.
In the preparation method provided by the invention, a bislactam unit is introduced into an acceptor-donor-acceptor (A-D-A) type acceptor molecule, and the purpose is to obtain an n-type non-fullerene acceptor material with good stability and high photoelectric conversion efficiency.
The condensed ring triazole bislactam-based non-fullerene acceptor material provided by the invention can be applied to the preparation of organic/polymer solar cells, organic photodetectors, organic field effect transistors, organic light emitting diodes and other organic electronic devices.
Further, the application of the condensed ring triazole bislactam-based non-fullerene acceptor material in the preparation of organic/polymer solar cells, organic photodetectors, organic field effect transistors, organic light emitting diodes and other organic electronic devices comprises the following steps: the condensed ring triazole bislactam-based non-fullerene acceptor material and the electron donor material are prepared into an active layer, and then the active layer is used in organic electronic devices such as organic/polymer solar cell devices and organic light detector devices.
Preferably, the polycyclic triazole bislactam-based non-fullerene acceptor material and the electron donor material are prepared into a photoelectric active layer for an organic/polymer solar cell device, an organic photodetector, an organic field effect transistor and an organic light-emitting diode device. The specific preparation process of the photoelectric active layer comprises the following steps: mixing the fused ring triazole bislactam base non-fullerene acceptor material with an electron donor material, adding a solvent to dissolve the mixture to obtain slurry, coating the slurry on conductive glass to prepare a film, and then preparing an organic/polymer solar cell device and an organic photodetector device. The solvent is at least one of chloroform, o-dichlorobenzene, tetrahydrofuran, dimethyltetrahydrofuran and trimethyltetrahydrofuran. The fused ring triazole bislactam non-fullerene acceptor material can be dissolved in a conventional organic solvent and has good processing performance.
Further, the application of the condensed ring triazole bislactam-based non-fullerene acceptor material in the preparation of organic/polymer solar cells, organic photodetectors, organic field effect transistors and organic light emitting diodes is provided; the electron donor material is an organic electron donor material; the electron donor material is at least one of PCE10, PCE12, P3HT and the like.
Preferably, the molar ratio of the condensed ring triazole bislactam-based non-fullerene acceptor material to the electron donor material is 1-1.5: 1.
More preferably, the electron donor materials are PCE10, PCE12, P3HT and other organic electron donor materials.
The organic/polymer solar cell and the organic photodetector device prepared by taking the condensed ring triazole dilactam non-fullerene acceptor material as the active layer both show excellent performance, the energy conversion efficiency of the organic photovoltaic cell is more than 11%, and the dark current density of the organic photodetector is lower than 10 -8 mA/cm 2 Fully shows that the non-fullerene acceptor material is used for organic photovoltaic and organic light detectionHas wide market prospect in the fields of devices and the like.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the preparation method of the fused ring triazole dilactam non-fullerene acceptor material provided by the invention has the advantages of strong universality of a synthesis method, mild synthesis conditions, high synthesis yield and the like, and can be popularized and applied to the amplification synthesis and production in the industry;
(2) the fused ring triazole dilactam non-fullerene acceptor material provided by the invention has a large pi conjugated skeleton of hetero atoms, can enhance the pi-pi interaction in molecules and among molecules, and improves the carrier mobility;
(3) the fused ring triazole bislactam non-fullerene acceptor material provided by the invention has stronger absorption in an ultraviolet-visible region (550-950nm), and belongs to a narrow band gap material (E) g ＜1.60eV)；
(4) According to the fused ring triazole bislactam group non-fullerene acceptor material provided by the invention, due to the introduction of a lactam group electron-deficient acceptor unit, the material has a lower HOMO energy level;
(5) the nitrogen atoms in the condensed rings of the condensed ring triazole dilactam non-fullerene receptor material provided by the invention not only serve as coplanar heteroatom bridges, but also can introduce side chains to increase the solubility of non-fullerene micromolecular receptors;
(6) the fused ring triazole bislactam non-fullerene acceptor material provided by the invention has wide commercial prospect in the organic electronic field such as organic photovoltaics, organic photodetectors and the like;
(7) the condensed ring triazole dilactam non-fullerene acceptor material provided by the invention is used as an active layer of a device, the energy conversion efficiency of an organic/polymer solar cell is more than 11%, and the dark current density of an organic photodetector is 10 -8 mA/cm 2 The advantages of the fused ring triazole bislactam-based non-fullerene acceptor materials are fully demonstrated below.
Drawings
FIG. 1 is an absorption spectrum of a solid-state thin film of fused ring triazole bislactam-based non-fullerene acceptor materials C1 and C2 on a quartz plate, which are prepared in example 1;
fig. 2 is a schematic structural diagram of an organic/polymer solar cell device and an organic photodetector device in which fused ring triazole bislactam group non-fullerene acceptor materials C1 and C2 prepared in examples 1 and 2 are organic active layers;
FIG. 3 is a J-V curve of an organic/polymer solar cell using the condensed ring triazole bislactam-based non-fullerene acceptor materials C1 and C2 prepared in examples 1 and 2 as organic active semiconductor layers;
FIG. 4 is an EQE-wavelength curve of the organic/polymer solar cell with the condensed ring triazole bislactam group non-fullerene acceptor materials C1 and C2 prepared in examples 1 and 2 as organic active semiconductor layers;
FIG. 5 is a J-V curve of an organic photodetector using the condensed ring triazole bislactam-based non-fullerene acceptor materials C1 and C2 prepared in examples 1 and 2 as organic active semiconductor layers;
fig. 6 is a specific detectivity-wavelength curve of an organic photodetector using the fused ring triazole bislactam based non-fullerene acceptor materials C1 and C2 prepared in examples 1 and 2 as organic active semiconductor layers.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples. The method is a conventional method unless otherwise specified. The starting materials are commercially available from the open literature unless otherwise specified. The reaction substrates used in the following examples, 5,10, 11-tris (2-ethylhexyl) -10, 11-dihydro-5H-thieno [2',3':4,5] pyrrolo [3,2-g ] thieno [3,2-b ] [1,2,3] thieno [4,5-e ] indole (a), N-chlorosuccinimide, 5, 6-difluoro-3- (dicyanomethylene) indolone (2FINCN), 5, 6-dichloro-3- (dicyanomethylene) indolone (2ClINCN), were purchased from Dongguan voltammetric photovoltaics, Inc., and the remaining reaction solvents used were commercially available. The room temperature, the normal temperature and unspecified temperature are all 20-35 ℃.
Detailed description of the preferred embodiment 1
A fused ring triazole bislactam radical non-fullerene acceptor material with a chemical structure of C1 is prepared by the following synthetic route:
(1) synthesis of an intermediate of formula B: under the protection of nitrogen, 5,10, 11-tri (2-ethylhexyl) -10, 11-dihydro-5H-thiophene [2',3':4,5] pyrrole [3,2-g ] thiophene [3,2-b ] [1,2,3] thiophene [4,5-e ] indole (a) (0.001mol), N-chlorosuccinimide (NCS) (0.02mol) and 0.07L of chloroform solvent are added into a three-necked bottle. After reacting for 10 hours at room temperature, extracting by dichloromethane, drying an organic phase by magnesium sulfate, and spin-drying the solvent to obtain a crude product. And purifying by a silica gel chromatographic column to obtain the target compound B, wherein the yield is 89%.
The structural characterization data is as follows,
MALDI-TOF-MS:m/z＝741.90(M + ).
as can be seen from the above, the compound has the correct structure and is the compound b shown.
(2) Synthesis of an intermediate of formula C: under the protection of nitrogen, 2,6, 6-tetramethylpiperidyl magnesium chloride lithium chloride complex (0.03mol) and 0.03L of tetrahydrofuran solution were added to a three-necked flask, and then placed at-30 ℃, compound B (0.001mol) was dissolved in 0.03L of tetrahydrofuran, added dropwise to the reaction flask, and then reacted at-30 ℃ for 12 hours. Propyl chloroformate (0.03mol) was then dissolved in 0.04L tetrahydrofuran solvent, added in portions to the above reaction flask, and transferred to room temperature for 12 hours. After the reaction is finished, hydrochloric acid is adopted for acidification, dichloromethane is adopted for extraction, an organic phase is dried by anhydrous magnesium sulfate, and a solvent is dried in a spinning mode to obtain a crude product. And purifying by a silica gel chromatographic column to obtain the target compound C, wherein the yield is 78%.
The structural characterization data is as follows,
MALDI-TOF-MS:m/z＝887.08(M + ).
as is clear from the above, the compound has a correct structure and is the compound c shown.
(3) Synthesis of an intermediate of formula D: under nitrogen protection, compound C (0.01mol), ammonium formate (0.03mol), palladium on carbon catalyst (0.03mmol) and 0.05L of ethanol solvent were added to a three-necked flask. Heating, refluxing, stirring and reacting for 24 hours, extracting by using dichloromethane, drying an organic phase by using anhydrous magnesium sulfate, and spin-drying a solvent to obtain a crude product. And purifying by a silica gel chromatographic column to obtain the target compound D, wherein the yield is 72 percent.
The structural characterization data is as follows,
MALDI-TOF-MS:m/z＝818.19(M + ).
as can be seen from the above, the compound has the correct structure and is the compound d shown.
(4) Synthesis of an intermediate of formula E: and sequentially adding the compound D (1mmol), liquid bromine (3mmol) and 0.03L of trichloromethane into a 25mL three-neck flask, heating and refluxing for 12 hours under the protection of nitrogen, cooling to room temperature, extracting by using dichloromethane, drying an organic phase by using anhydrous magnesium sulfate, and spin-drying a solvent to obtain a crude product. And purifying by a silica gel chromatographic column to obtain the target compound E, wherein the yield is 80%.
MALDI-TOF-MS:m/z＝975.99(M + ).
As can be seen from the above, the compound has the correct structure and is the compound e shown.
(5) Synthesis of an intermediate of formula F: under nitrogen protection, compound E (1mmol), sodium hydroxide (3mmol), ethanol (0.03L), tetrahydrofuran (0.03L), and water (0.03L) solvent were added to a three-necked flask. After 12 hours of reflux, cool to room temperature. Extracting with dichloromethane, drying the organic phase with anhydrous magnesium sulfate, and spin-drying the solvent to obtain a crude product. And purifying by a silica gel chromatographic column to obtain the target compound F, wherein the yield is 88%.
MALDI-TOF-MS:m/z＝891.82(M + ).
As can be seen from the above, the compound has the correct structure and is the compound F.
(6) Synthesis of an intermediate of formula G: under nitrogen protection, a single-neck flask was charged with compound F (1mmol), oxalyl chloride (3mmol), dichloromethane (0.03L), and 2mL of N, N' -Dimethylformamide (DMF) solvent, and reacted at room temperature for 12 hours. Then, the solvent was removed, N- (2-ethylhexyl) thiophen-3-amine (3mmol), triethylamine (2mL) and 0.02L of dichloromethane solvent were added and mixed well, and reacted at room temperature for 12 hours. Extracting by adopting dichloromethane, drying an organic phase by using anhydrous magnesium sulfate, and spin-drying a solvent to obtain a crude product. And purifying by a silica gel chromatographic column to obtain the target compound G, wherein the yield is 80%.
MALDI-TOF-MS:m/z＝1278.53(M + ).
As can be seen from the above, the compound has the correct structure and is the compound G shown.
(7) Synthesis of an intermediate of formula H: under nitrogen protection, compound G (1mmol) and tricyclohexylphosphine fluoborate (PCy) were added to a single-neck flask 3 ·HBF 4 ) (10mmol), palladium acetate (10mmol), cesium carbonate (10mmol) and 0.04L of N, N' -Dimethylformamide (DMF) solvent, refluxed for 24 hours and then cooled to room temperature. Extracting with dichloromethane, drying the organic phase with anhydrous magnesium sulfate, and spin-drying the solvent to obtain a crude product. And purifying by a silica gel chromatographic column to obtain the target compound H, wherein the yield is 75%.
MALDI-TOF-MS:m/z＝1116.70(M + ).
As can be seen from the above, the compound has the correct structure and is the compound h shown.
(8) Synthesis of intermediates of the formula I: compound H (0.001mol), phosphorus oxychloride (0.01mol) and 0.04L of N, N' -Dimethylformamide (DMF) solvent were added to a three-necked flask under nitrogen. After 12 hours of reflux, cool to room temperature. Extracting with dichloromethane, drying the organic phase with anhydrous magnesium sulfate, and spin-drying the solvent to obtain a crude product. Purifying by silica gel chromatographic column to obtain the target compound I, wherein the yield is 90%.
MALDI-TOF-MS:m/z＝1172.72(M + ).
From the above, the compound has a correct structure and is the compound I shown.
(7) Synthesizing a fused ring triazole bislactam-based non-fullerene acceptor material with a chemical structural formula of C1: under nitrogen protection, compound i (0.001mol), 5, 6-difluoro-3- (dicyanomethylene) indolone (2FINCN) (0.003mol), pyridine (0.001mol) and 0.04L of chloroform solvent were added to a three-necked flask. After refluxing for 12 hours, it was cooled to room temperature. Extracting with dichloromethane, drying the organic phase with anhydrous magnesium sulfate, and spin-drying the solvent to obtain a crude product. Purifying by silica gel chromatography to obtain the target compound C1 with the yield of 90%.
MALDI-TOF-MS:m/z＝1597.04(M + ).
From the above, the compound has a correct structure and is shown as a fused ring triazole bislactam-based non-fullerene acceptor material C1.
Specific example 2
A fused ring triazole bislactam radical non-fullerene acceptor material with a chemical structure of C2 is prepared by the following synthetic route:
the experimental steps of the fused ring triazole bislactam-based non-fullerene acceptor material C2 are basically the same as those of example 1, and the compound I is prepared according to the experimental steps of example 1; and reacting the compound I with 5, 6-dichloro-3- (dicyanomethylene) indolone (2ClINCN) to obtain the fused ring triazole bislactam non-fullerene acceptor material C2.
Synthesizing a fused ring triazole bislactam-based non-fullerene acceptor material with a chemical structural formula of C2: under nitrogen, compound I (0.001mol), 5, 6-dichloro-3- (dicyanomethylene) indolone (2ClINCN) (0.003mol), pyridine (0.001mol) and 0.04L of chloroform solvent were added to a three-necked flask. After refluxing for 12 hours, it was cooled to room temperature. Extracting with dichloromethane, drying the organic phase with anhydrous magnesium sulfate, and spin-drying the solvent to obtain a crude product. Purifying by silica gel chromatography to obtain the target compound C2 with the yield of 85%.
MALDI-TOF-MS:m/z＝1662.85(M + ).
From the above, the compound has a correct structure and is shown as a fused ring triazole bislactam-based non-fullerene acceptor material C2.
The spectral properties of the fused ring triazole bislactam based non-fullerene acceptor materials C1 and C2 and the properties of the polymer solar cell and the organic photodetector, which are prepared in the above examples 1 and 2, are measured:
(1) absorption spectrum property of fused ring triazole bislactam group non-fullerene acceptor material C1
FIG. 1 shows that condensed ring triazole bislactam group is not richUltraviolet-visible-near infrared absorption spectra of thin films of the leylen acceptor materials C1 and C2 on a quartz plate (thin films prepared by spin coating a chloroform solution on a quartz plate). As can be seen from FIG. 1, the fused ring triazole bislactam based non-fullerene acceptor materials C1 and C2 both exhibit a wide absorption range, the absorption maximum absorption side bands of the films are about 911nm and 945nm, respectively, and the corresponding optical band gaps are 1.36eV and 1.31eV (the optical band gaps are according to the formula E) g 1240/λ calculation, where E g Is the optical band gap and lambda is the absorption maximum side band value of the film).
(2) Performance determination of polymer photovoltaic cell of fused ring triazole bislactam-based non-fullerene acceptor materials C1 and C2
The semiconductor characteristics of the condensed ring triazole dilactam-based non-fullerene acceptor material film are researched by adopting a bulk heterojunction organic/polymer solar cell structure, and the device structure is shown in figure 2. The detailed device construction procedure is completed with reference to the literature (Sci China Chem,2019,62: 746-. Taking Indium Tin Oxide (ITO) glass with the square resistance of 10 omega, sequentially using acetone, a detergent, deionized water and isopropanol for ultrasonic cleaning, and carrying out plasma treatment for 10 minutes; spin-coating a film of Polyethoxythiophene (PEDOT) doped with polystyrene sulfonic acid (PSS) (PEDOT: PSS ═ 1:6, w/w) on ITO, drying the film of PEDOT: PSS with a thickness of 30nm in a vacuum oven at 80 ℃ for 8 hours; then C1&C2: a solution of PCE10 ═ 1:1.5w/w in chlorobenzene (2 wt.%) was spin coated onto the surface of PEDOT: PSS films (PCE10, available from guan volt ampere-optical technology ltd) with a thickness of 100nm as the active layer; then a layer of Ca with the thickness of 10nm is evaporated on the active layer, and finally a layer of metal Ag with the thickness of about 100nm is evaporated, and the structure of the device is as follows: ITO/PEDOT PSS/active eye (C1)&C2) The method comprises the following steps PCE 10/Ca/Ag. Simulated sunlight light source combined by 500W xenon lamp and AM 1.5 filter (light intensity is 100 mW/cm) 2 ) Next, the J-V curve measurement was performed using a Keithley 2602 digital source table, and the curve is shown in FIG. 3. The test results are shown in fig. 3: condensed ring triazole bislactam-based non-fullerene acceptor material C1 short-circuit current J sc Is 22.2mA/cm 2 Open circuit voltage V oc 0.92V and a fill factor FF of 66.5%, from which the energy conversion efficiency of the cell was calculated to be 136 percent; condensed ring triazole bislactam-based non-fullerene acceptor material C2 short-circuit current J sc Is 21.5mA/cm 2 Open circuit voltage V oc At 0.84V, the fill factor FF was 64.1%, from which the energy conversion efficiency of the battery was calculated to be 11.6%; and the fused ring triazole bislactam-based non-fullerene acceptor materials C1 and C2 have wider External Quantum Efficiency (EQE) from 300nm to 950nm, and the EQE curve is shown in FIG. 4.
(3) Organic photodetector performance determination of condensed ring triazole bislactam-based non-fullerene acceptor materials C1 and C2
The semiconductor characteristics of the condensed ring triazole dilactam-based non-fullerene acceptor material film are researched by adopting a device structure shown in figure 2. The preparation method of the device is consistent with that of the organic/polymer solar cell, and specifically comprises the following steps: taking Indium Tin Oxide (ITO) glass with the square resistance of 10 omega, sequentially using acetone, a detergent, deionized water and isopropanol for ultrasonic cleaning, and carrying out plasma treatment for 10 minutes; spin-coating a film of Polyethoxythiophene (PEDOT) doped with polystyrene sulfonic acid (PSS) (PEDOT: PSS ═ 1:6, w/w) on ITO, drying the film of PEDOT: PSS with a thickness of 30nm in a vacuum oven at 80 ℃ for 8 hours; then C1&C2: a chlorobenzene solution (2 wt.%) of PCE10 ═ 1:1.5w/w was spin-coated on the surface of the PEDOT: PSS film to a thickness of 100nm as an active layer; then a layer of Ca with the thickness of 10nm is evaporated on the active layer, and finally a layer of metal Ag with the thickness of about 100nm is evaporated, and the structure of the device is as follows: ITO/PEDOT PSS/active eye (C1)&C2) The method comprises the following steps PCE 10/Ca/Ag. The current-voltage data of the device was obtained with a current voltage source (Keithley 2602) under 650nm illumination, the curve of which is shown in fig. 5. The test results are shown in fig. 5: dark current J of device with condensed ring triazole bislactam-based non-fullerene acceptor material C1 as active layer under-1V sc Is 1.9X 10 -9 mA/cm 2 (ii) a Dark current J of device with condensed ring triazole bislactam-based non-fullerene acceptor material C2 as active layer under-1V sc Is 5.8 multiplied by 10 -9 mA/cm 2 . In order to research the specific detectivity of the device, a specific detectivity-wavelength curve (shown in FIG. 6) is obtained through calculation, and the specific detectivity of the devices C1 and C2 exceeds 10 in the working waveband of 450-850 nm 11 Jones。
Furthermore, the results of the study obtained confirm that: the condensed ring triazole dilactam non-fullerene acceptor material shown in the formula (I) is an organic material with excellent comprehensive performance; the condensed ring triazole bislactam group non-fullerene acceptor material has a large coplanar framework, a strong heteroatom effect and good solution processability; the material has excellent device performance in organic/polymer solar cells and organic photodetectors, the photoelectric conversion efficiency is more than 11%, and the dark current density is 10 -8 mA/cm 2 The following. The preparation method provided by the invention has the advantages of simplicity, effectiveness, easily available raw materials, strong popularization and the like. By changing different solubilizing alkyl chains and end group groups, a series of fused ring triazole bislactam group non-fullerene receptor materials with excellent comprehensive performance can be prepared, which has very important significance for researching the internal relation between the structure and the performance of the fused ring triazole bislactam group non-fullerene receptor materials and has guiding significance for developing high-performance non-fullerene receptor materials in the future.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A condensed ring triazole bislactam group non-fullerene acceptor material is characterized in that the structural formula is as follows:
wherein R is 1 Is C 1 -C 20 Alkyl groups of (a);
ar is a thiophene group, a bithiophene group or a bithiophene derivative group;
EG is any one of the following groups:
wherein R is 2 Is a hydrogen atom, a halogen substituent, C 1 -C 20 Alkyl of (C) 1 -C 20 Alkoxy or cyano of (a).
2. The fused ring triazole bislactam-based non-fullerene acceptor material of claim 1, wherein: ar is the following group:
the dotted line is the connection location.
3. A preparation method of the condensed ring triazole bislactam-based non-fullerene acceptor material according to any one of claims 1 to 2, characterized by comprising the following steps:
(1) under the protection of nitrogen, reacting a condensed ring triazole compound A with N-chlorosuccinimide to obtain a compound B; the structural formulas of the condensed ring triazole compound A and the compound B are respectively as follows:
wherein R is 1 Is as defined in claim 1;
(2) under the protection of nitrogen, reacting the compound B with propyl chloroformate to obtain a compound C, wherein the structural formula of the compound C is as follows:
wherein R is 1 Is as defined in claim 1;
(3) reacting the compound C with ammonium formate under the action of a palladium-carbon catalyst to obtain a compound D, wherein the structural formula of the compound D is as follows:
wherein R is 1 Is as defined in claim 1;
(4) under the protection of inert gas, reacting the compound D with liquid bromine to obtain a compound E, wherein the structural formula of the compound E is as follows:
wherein R is 1 Is as defined in claim 1;
(5) and (2) carrying out hydrolysis reaction on the compound E and sodium hydroxide to obtain a compound F, wherein the structural formula of the compound F is as follows:
wherein R is 1 Is as defined in claim 1;
(6) reacting the compound F with oxalyl chloride and N-alkyl thiophene derivative-3-amine to obtain a compound G, wherein the structural formula of the compound G is as follows:
wherein R is 1 And Ar is as defined in claim 1;
(7) the compound G, tricyclohexylphosphine fluoborate, palladium acetate and cesium carbonate act to obtain a compound H, and the structural formula of the compound H is as follows:
wherein R is 1 And Ar is as defined in claim 1;
(9) the compound H is subjected to Vilsmeier-Haack reaction to obtain a compound I, wherein the structural formula of the compound I is as follows:
wherein R is 1 And Ar is as defined in claim 1;
(10) reacting the compound I with EG ketone through Knoevenagel to obtain a target fused ring triazole bislactam group non-fullerene receptor material;
the EG ketone is any one of the following structures:
wherein R is 2 Is a hydrogen atom, a halogen substituent, C 1 -C 20 Alkyl of (C) 1 -C 20 Alkoxy or cyano of (2).
4. The preparation method of the fused ring triazole bislactam-based non-fullerene acceptor material according to claim 3, which is characterized by comprising the following steps:
(1) uniformly mixing a fused ring triazolyl compound A, N-chlorosuccinimide and a chloroform solvent, stirring at room temperature for reacting for 1-24 hours, and purifying reaction liquid to obtain a compound B;
(2) uniformly mixing a compound B, a 2,2,6, 6-tetramethyl piperidyl lithium chloride magnesium chloride compound and a tetrahydrofuran solvent, dissolving propyl chloroformate in a dried tetrahydrofuran solution after the reaction is finished, adding the propyl chloroformate into the reaction in batches, and purifying the reaction solution obtained after the reaction is finished to obtain a compound C;
(3) uniformly mixing the compound C, ammonium formate, a palladium-carbon catalyst and an ethanol solvent, refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, and purifying reaction liquid to obtain a compound D;
(4) uniformly mixing the compound D, liquid bromine and a trichloromethane solvent, then refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, and purifying the reaction solution to obtain a compound E;
(5) uniformly mixing the compound E, sodium hydroxide, ethanol, tetrahydrofuran and water, then refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, adding hydrochloric acid into reaction liquid for acidification, and purifying to obtain a compound F;
(6) uniformly mixing a compound F, oxalyl chloride, dichloromethane and a little N, N' -dimethylformamide solvent, stirring at room temperature for reaction for 1-24 hours, removing the solvent, adding N-alkyl thiophene derivative-3-amine, triethylamine and dichloromethane solvent, uniformly mixing, stirring at room temperature for reaction for 1-24 hours, and purifying to obtain a compound G;
(7) uniformly mixing a compound G, tricyclohexylphosphine fluoborate, palladium acetate, cesium carbonate and an N, N' -dimethylformamide solvent, then refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, and purifying reaction liquid to obtain a compound H;
(8) uniformly mixing a compound H, phosphorus oxychloride and an N, N' -dimethylformamide solvent, refluxing, stirring, reacting for 1-24 hours, cooling to room temperature, and purifying reaction liquid to obtain a compound I;
(9) uniformly mixing the compound I, EG ketone, pyridine and a chloroform solvent, then refluxing, stirring and reacting for 1-24 hours, cooling to room temperature, and purifying the reaction solution to obtain the target fused ring triazole bislactam non-fullerene acceptor material.
5. The preparation method of the fused ring triazole bislactam-based non-fullerene acceptor material according to claim 4, wherein the molar ratio of the fused ring triazole based compound A in the step (1) to N-chlorosuccinimide is 1:1-100, and the molar volume ratio of the fused ring triazole based compound A in the step (1) to a chloroform solvent is 1mol: 0.01-1L; the molar ratio of the compound B to the 2,2,6, 6-tetramethyl piperidyl magnesium chloride lithium chloride compound in the step (2) is 1:2-100, the molar ratio of the compound B to propyl chloroformate is 1:2-100, and the molar volume ratio of the compound B to the tetrahydrofuran solvent in the step (2) is 1mol: 0.01-1L; the compound C in the step (3): ammonium formate: the mole ratio of the palladium carbon catalyst is 1: 2-100: 0.01-0.1, wherein the molar volume ratio of the compound C to the ethanol solvent in the step (3) is 1mol: 0.01-1L; the molar ratio of the compound D and liquid bromine in the step (4) is 1:2-100, and the molar volume ratio of the compound D and a chloroform solvent in the step (4) is 1mol: 0.01-1L; the molar ratio of the compound E to the sodium hydroxide in the step (5) is 1:2-100, and the compound E in the step (5): ethanol: tetrahydrofuran: the molar volume ratio of the water solvent is 1mol:0.01-1L:0.01-1L: 0.01-1L.
6. The preparation method of the fused ring triazole bislactam-based non-fullerene acceptor material according to claim 4, wherein the compound F in the step (6): the mole ratio of oxalyl chloride is 1:2-100, step (6) compound F: the molar ratio of the N-alkyl thiophene derivative-3-amine is 1:2-100, and the molar volume ratio of the compound F to the N, N' -dimethylformamide solvent in the step (6) is 1mol: 0.01-1L; the molar volume ratio of the compound F to the dichloromethane solvent in the step (6) is 1mol: 0.01-1L; the molar volume ratio of the compound F to the triethylamine solvent in the step (6) is 1mol: 0.01-1L; step (7) compound G: tricyclohexylphosphine borofluoride: palladium acetate: the mol ratio of the cesium carbonate is 1: 2-100: 2-100: 2-100: 2-100; the molar volume ratio of the compound F to the N, N' -dimethylformamide solvent in the step (7) is 1mol: 0.01-1L; the molar ratio of the compound H to the phosphorus oxychloride in the step (8) is 1: 1-100; the molar volume ratio of the compound H to the N, N' -dimethylformamide solvent in the step (8) is 1mol: 0.01-1L; the molar ratio of the compound I to EG ketone in the step (9) is 1: 3-100; the molar ratio of the compound I to the pyridine in the step (9) is 1: 1-100; the molar volume ratio of the compound H to the chloroform solvent in the step (9) is 1mol: 0.01-1L.
7. The preparation method of the fused ring triazole bislactam non-fullerene acceptor material according to claim 4, wherein the temperature of the first reaction in the step (2) is-20 to-30 ℃, the reaction time is 1 to 24 hours, the temperature of the second reaction is normal temperature, and the reaction temperature is 1 to 24 hours;
in the steps (3) - (5) and (7) - (9), the temperature for reflux stirring reaction is 60-200 ℃.
8. The application of the condensed ring triazole bislactam-based non-fullerene acceptor material of claim 1 in preparation of organic/polymer solar cells and organic photodetectors.
9. The application of the condensed ring triazole bislactam-based non-fullerene acceptor material according to claim 8 in preparation of organic/polymer solar cells and organic photodetectors, wherein the application comprises the following steps: preparing a condensed ring triazole bislactam-based non-fullerene acceptor material and an electron donor material into an active layer, preparing the condensed ring triazole bislactam-based non-fullerene acceptor material and the electron donor material into the active layer, and then using the active layer in an organic/polymer solar cell device and an organic photodetector device.
10. The application of the condensed ring triazole bislactam-based non-fullerene acceptor material in preparation of organic/polymer solar cells and organic photodetectors according to claim 8, wherein the electron donor material is at least one of PCE10, PCE12 and P3 HT:
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